Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Search
Advanced search
OR
Browse
Search
Volume 59, Issue 4
Displaying 1-24 of 24 articles from this issue
Show all abstracts
    • |<
    • <
    • 1
    • >
    • >|
Review
  • Approaches to Neural Stem Cells and Cancer Cells Based on Natural Products
    Midori A. Arai
    Article type: Review
    2011 Volume 59 Issue 4 Pages 417-426
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.417
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    We have developed “protein- and cell-based screen methods” for the isolation of new natural products. By using VDR (vitamin D receptor) immobilized magnetic beads, two new natural products were isolated rapidly. To find inhibitors of Hes1 protein, which is one of the important transcriptional factors in neural stem cells, a Hes1 dimer plate assay was developed, and then first Hes1 dimer inhibitors were found from our natural products library. As a “cell-based screen method,” a reporter gene assay for screening Hh (hedgehog) signaling inhibitors was constructed. New Hh signaling inhibitors were isolated from our natural extracts library. We evaluated their Hh inhibitory activity in Hh related protein synthesis and cytotoxicity against cancers, in which Hh signaling is aberrantly activated. In addition to the naturally made compounds library (extracts library), “small molecules based on natural products” were synthesized. The total synthesis of Melleumin A, B, which were isolated by our group, was achieved. From their synthetic derivatives, inhibitors of the Wnt signal, which has been reported to cause colon cancers, were discovered. Moreover, flavanone and chromone were selected as natural product scaffolds. Many flavonoids and chromones with diverse heterocyclic units were constructed using our efficient synthetic method.
    View full abstract
    Download PDF (1916K)
Regular Articles
  • Solid Dispersions of Carvedilol with Porous Silica
    Borut Kovačič, Franc Vrečer, Odon Planinšek
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 427-433
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.427
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Solid dispersion particles of carvedilol (CAR) were prepared with porous silica (Sylysia 350) by the solvent evaporation method in a vacuum evaporator to ensure an effective pore-filling procedure. Two sets were prepared, each with various amounts of CAR in solid dispersions, and with the pore-filling process differing each time. Set A was prepared by a one-step filling method and set B by a multiple-step pore-filling method of CAR into porous silica. The solid dispersions were then characterized using thermal analysis, X-ray diffraction, and nitrogen adsorption experiments. The results showed that the drug release can be significantly improved compared with the dissolution of the drug in its pure crystalline or amorphous state. Drug release from solid dispersion was faster when the drug content in the solid dispersion was low, which enabled the drug to be finely dispersed along the hydrophilic carrier's surface. The results also showed that a multiple-step pore-filling procedure is more effective for drug loading as indicated by the absence of a crystalline drug state, greatly reduced porosity, and improved wettability and physical stability of the amorphous CAR.
    View full abstract
    Download PDF (2519K)
  • Influence of Swallowing Aids on the Adsorption and Palatability of Kremezin®
    Miyako Yoshida, Mai Hazekawa, Tamami Haraguchi, Takahiro Uchida
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 434-437
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.434
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    The purpose of this study was to evaluate the effect of three swallowing aids on the adsorbent properties and palatability of a mixture of the oral charcoal adsorbent, Kremezin®. None of the swallowing aids had any effect on the adsorption of indole by Kremezin®, either in vitro and in vivo. In gustatory sensation tests of the palatability of the swallowing aids with Kremezin®, 14 items were evaluated according to the semantic differential (SD) method. Factor analysis of the results identified two main factors ‘Remaining after removing from mouth’ and ‘Sense of holding in mouth’ as predominantly determining the palatability. The swallowing aid with the highest viscosity allowed the best dispersion of Kremezin®, and also improved the palatability of Kremezin® the most.
    View full abstract
    Download PDF (1209K)
  • Solubility, Dissolution Rate and Bioavailability Enhancement of Irbesartan by Solid Dispersion Technique
    Rikisha Jaysukhbhai Boghra, Pranita Chandrakant Kothawade, Veena Shail ...
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 438-441
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.438
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    The objective of present work was to enhance the solubility and bioavailability of poorly aqueous soluble drug Irbesartan (IBS). The solid dispersions were prepared by spray drying method using low viscosity grade HPMC E5LV. Prepared solid dispersions were characterized by dissolution study, fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), differential scanning calorimetry (DSC) and X-ray diffraction studies (XRD). Results of the SEM, DSC and XRD study showed the conversion of crystalline form of IBS to amorphous form. The dissolution rate was remarkably increased in case of solid dispersion compared to pure IBS. Solubility and stability of solid dispersion was increased due to surfactant and wetting property, slowing devitrification and having anti-plasticization effect of HPMC E5LV. In vivo studies were performed in healthy rabbits (New Zealand grey) and compared with plain IBS. Solid dispersions showed increase in relative bioavailability than the plain IBS suspension. In conclusion, the prepared solid dispersions showed remarkable increase in solubility, dissolution rate and hence bioavailabilty of poorly water soluble drug Irbesartan.
    View full abstract
    Download PDF (1368K)
  • Quantification of Pharmaceutical Polymorphs and Prediction of Dissolution Rate Using Theophylline Tablet by Terahertz Spectroscopy
    Jin Hisazumi, Tatsuya Suzuki, Hiroaki Nakagami, Katsuhide Terada
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 442-446
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.442
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Theophylline has an anhydrous form and a monohydrated form, and the dissolution rate of the anhydrous form is higher than that of the monohydrated form. Terahertz (THz) spectra of theophylline tablet containing the theophylline anhydrous form, monohydrated form, microcrystalline cellulose and magnesium stearate exhibited a specific absorption peak at 0.96 THz, where the theophylline anhydrous form demonstrated an absorption peak. Additionally, the intensity of the peak at 0.96 THz gradually decreased as the proportion of the anhydrous form decreased. The multivariate data analysis was performed to correlate the THz spectra of theophylline tablets with the ratio of the theophylline anhydrous form. The calibration model used to predict the mixing ratio of the theophylline anhydrous form from the THz spectra achieved root-mean-squared errors of cross-validation (RMSECV) of 2.89%, a slope of 0.9934 and an R2 of 0.9927. In addition, there were intentions to develop a prediction model for the dissolution rate of theophylline from the drug product. The dissolution rate of theophylline tablet was gradually delayed as the proportion of the anhydrous form was decreased. The multivariate data analysis was performed to correlate the THz spectra of theophylline tablets with the dissolution rate. The calibration model used to predict the percentage of theophylline dissolved in 45 min from the THz spectra achieved an RMSECV of 3.29%, a slope of 0.9260 and an R2 of 0.9423. Furthermore, there were no significant differences between the predicted and measured percentages of theophylline dissolved in 45 min in the theophylline tablets that were stored at 84% relative humidity (RH) and 25 °C for 12 h or 3 d.
    View full abstract
    Download PDF (685K)
  • Benzamides and Quinazolines from a Mangrove Actinomycetes Streptomyces sp. (No. 061316) and Their Inhibiting Caspase-3 Catalytic Activity in Vitro
    Guodong Chen, Hao Gao, Jinshan Tang, Yuanfan Huang, Ying Chen, Ying Wa ...
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 447-451
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.447
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    One new benzamide, 3-hydroxyl-2-N-iso-butyryl-anthranilamide (1), together with two known benzamides (2, 3) and three known quinazolines (4—6), was isolated from a mangrove actinomycetes Streptomyces sp. (No. 061316), which displayed inhibiting Caspase-3 activity in vitro. The structure of 1 was elucidated by electrospray ionization (ESI)-MS, NMR spectroscopies and X-ray crystal diffraction. After evaluation of all compounds for their inhibitory effect on Caspase-3 in vitro, 3-hydroxyl-anthranilamide (2) and 8-hydroxyl-2,4-dioxoquinazoline (6) showed activity against Caspase-3 with IC50 values of 32 and 36 μM, respectively.
    View full abstract
    Download PDF (553K)
  • Resveratrol Derivatives from Vatica albiramis
    Naohito Abe, Tetsuro Ito, Masayoshi Oyama, Ryuichi Sawa, Yoshikazu Tak ...
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 452-457
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.452
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Three new stilbene derivatives, albiraminols A (1) (resveratrol hexamer), B (2) (resveratrol dimer), and vatalbinoside F (3) (mono-glucoside of resveratrol dimer), along with malibatol were isolated from acetone soluble portions of the stem of Vatica albiramis. The structures of the isolates were established on the basis of spectroscopic analyses, including a detailed NMR spectroscopic investigation. The biosynthetic aspects of the isolates are discussed in this paper. Compound 1 is composed of tetrameric resveratrol (vaticanol B (1A)) and dimeric resveratrol (1B) and is the first instance of the resveratrol derivative bearing a 5,6,11,12-tetrahydro-5,11-epoxydibenzo[a,e][8]annulene ring system. Compound 2 possesses a novel 4,5-dihydro-13-oxabenzo[3,4]azuleno[7,8,1-jkl]phenanthrene skeleton in the framework.
    View full abstract
    Download PDF (957K)
  • Phragmalin-Type Limonoid Orthoesters from the Twigs of Swietenia macrophylla
    Bing-Dong Lin, Chuan-Rui Zhang, Sheng-Ping Yang, Yan Wu, Jian-Min Yue
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 458-465
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.458
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Eleven new phragmalin-type limonoids, swietenitins N—X (1—11), together with a known one, epoxyfebrinin B (12), were isolated from the twigs of Swietenia macrophylla. The structures of the new compounds were established on the basis of spectroscopic methods, and that of compound 1 was confirmed by single-crystal X-ray diffraction. The stereochemistry of epoxyfebrinin B (12) was fully assigned in this study.
    View full abstract
    Download PDF (1136K)
  • Medicinal Plants of Thailand. I Structures of Rheedeiosides A—D and cis-Entadamide A β-D-Glucopyranoside from the Seed Kernels of Entada rheedei
    Sachiko Sugimoto, Katsuyoshi Matsunami, Hideaki Otsuka
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 466-471
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.466
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Four new oleanane-type triterpene oligoglycosides, named rheedeiosides A, B, C and D, and one new thioamide glycoside, cis-entadamide A β-D-glucopyranoside, were isolated from the seed kernels of a Thai medicinal plant, Entada rheedei SPRENGEL. The rheedeiosides were found to contain N-acetylglucosamine as a sugar component. Their structures were elucidated based on spectral and chemical evidence.
    View full abstract
    Download PDF (672K)
  • 2-Aryl-1,4-naphthoquinone-1-oxime Methyl Ethers: Their Cytotoxic Activity
    Tsutomu Ishikawa, Tatsuru Saito, Ayako Kurosawa, Toshiko Watanabe, Sak ...
    Article type: Regular Article
    2011 Volume 59 Issue 4 Pages 472-475
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.472
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Preliminary examination for the structure–activity relationship of quinone monooxime derivatives on cytotoxicity against HeLa S3 cell and further trials using eight different cell lines suggested that 2-aryl-6,7-methylenedioxy-1,4-naphthoquinone-1-oxime methyl ethers, carrying 2-methoxy-4,5-methylenedioxyphenyl, 7-methoxy-2-methylbenzofuran-4-yl, and 2-methoxycarbonyl-3,4-dimethoxyphenyl as the 2-aryl substituent, were potential candidates for anti-cancer drugs.
    View full abstract
    Download PDF (545K)
Notes
  • Potential Use of Polypseudorotaxanes of Pegylated Polyamidoamine Dendrimer with Cyclodextrins as Novel Sustained Release Systems for DNA
    Keiichi Motoyama, Kayoko Hayashida, Hidetoshi Arima
    Article type: Note
    2011 Volume 59 Issue 4 Pages 476-479
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.476
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    In this study, we demonstrated the potential use of polypseudorotaxanes (PPRXs) of polyethylene glycol (PEG, molecular weight: 2000)-grafted polyamidoamine dendrimer (PEG-dendrimer) with cyclodextrins (CyDs) as novel sustained release systems for plasmid DNA (pDNA). PEG-dendrimer/pDNA complex formed PPRXs with α-CyD and γ-CyD solutions, but not with β-CyD solution. In the PEG-dendrimer/CyDs PPRXs systems, 17.9 mol of α-CyD and 8.8 mol of γ-CyD were involved in the PPRXs formation with one PEG chain by α-CyD and γ-CyD, respectively. In addition, the CyDs PPRX formation provided the sustained release of pDNA from PEG-dendrimer complex with pDNA at least 72 h in vitro. In addition, the release of pDNA from CyDs PPRX retarded as the dissolution medium volume decreased. These results suggest that the PEG-dendrimer/CyD PPRX systems can work as a sustained DNA release system, and the PPRX formation with CyDs may be useful as a sustained drug delivery technique for other pegylated polymers.
    View full abstract
    Download PDF (1066K)
  • Novel Prenyl Bibenzyls from the New Zealand Liverwort Marsupidium epiphytum
    Masao Toyota, Ikuko Omatsu, John Braggins, Yoshinori Asakawa
    Article type: Note
    2011 Volume 59 Issue 4 Pages 480-483
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.480
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    The ether extract of the New Zealand liverwort Marsupidium epiphytum gave four new prenyl bibenzyl derivatives, along with a known prenyl bibenzyl derivative which has been isolated from the Ecuadorian liverwort Lethocolea glossophylla; their structures were determined by 2D-NMR spectrum. The chemical constituents of Marsupidium epiphytum are highly characteristic since they elaborate dihydrooxepin type compounds and prenyl type bibenzyls. These structures are closely related to those found in Radula spp. (Radulaceae), although bibenzyls with two prenyl groups have not been isolated from the Radula spp. Although Marsupidium spp. are different from Radula spp. morphologically, the constituents are closely related. This is the first example of isolation of prenyl bibenzyl derivatives from M. epiphytum, a species which has not previously been investigated phytochemically.
    View full abstract
    Download PDF (510K)
  • Pterisolic Acids A—F, New ent-Kaurane Diterpenoids from the Fern Pteris semipinnata
    Fei Wang, Ya-Ju Li, Fu-Cai Ren, Guo-Zhu Wei, Ji-Kai Liu
    Article type: Note
    2011 Volume 59 Issue 4 Pages 484-487
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.484
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Six new ent-15-oxokauran-19-oic acid derivatives, named pterisolic acids A—F (1—6), were isolated from the ethanol extract of the fern Pteris semipinnata (Pteridaceae), and the structures of these new ent-kauranoids were elucidated on the basis of extensive spectroscopic studies and single crystal X-ray diffraction analysis.
    View full abstract
    Download PDF (693K)
  • Synthetic Studies on (+)-Biotin, Part 15: A Chiral Squaramide-Mediated Enantioselective Alcoholysis Approach toward the Total Synthesis of (+)-Biotin
    Xu-Xiang Chen, Fei Xiong, Han Fu, Zhi-Qian Liu, Fen-Er Chen
    Article type: Note
    2011 Volume 59 Issue 4 Pages 488-491
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.488
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    An efficient stereocontrolled total synthesis of (+)-biotin (1) has been achieved via the intermediacy of Roche's lactone 5 starting from cis-1,3-dibenzyl-2-imidazole-4,5-dicarboxylic acid (2). The bifunctional cinchona alkaloid-derived squaramide-promoted enantioselective alcoholysis was utilizing as a tool for the construction of two contiguous stereocenters of C-3a and C-6a in biotin molecular with excellent enantioselectivity. In addition, the 4-carboxybutyl side chain was assembled by first using C4+C1 approach via a novel tricyclic thiophanium salt intermediate.
    View full abstract
    Download PDF (581K)
  • Three New Highly Acylated 3,4-seco-Grayanane Diterpenoids from the Fruits of Pieris formosa
    Zhao-Yuan Wu, Yuan-Dan Li, Gui-Sheng Wu, Huai-Rong Luo, Hong-Mei Li, R ...
    Article type: Note
    2011 Volume 59 Issue 4 Pages 492-495
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.492
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Phytochemical investigation on the fruits of Pieris formosa resulted in the isolation of three new highly acylated 3,4-seco-grayanane diterpenoids, pierisformotoxins E—G (1—3). Their structures were elucidated on the basis of extensive spectroscopic analysis, including 1D-, 2D-NMR, electrospray ionization-mass spectra (ESI-MS) and high resolution (HR)-MS.
    View full abstract
    Download PDF (691K)
  • Triterpenoids and Diterpenoids from Viburnum chingii
    Xuan-Qin Chen, Yan Li, Juan He, Xiao Cheng, Kou Wang, Ming-Ming Li, Zh ...
    Article type: Note
    2011 Volume 59 Issue 4 Pages 496-498
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.496
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Two new oleanane triterpenoids (1—2) and one new vibsane-type diterpenoid (3), together with 7 known compounds (4—10), were isolated from the leaves of Viburnum chingii. The structures of compounds 1—3 were elucidated by means of spectroscopic methods including extensive 1D- and 2D-NMR technique. Cytotoxicity of compounds 1—10 were tested against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 cell lines. Compound 3 showed significant cytotoxicity against HL-60, SK-BR-3, and PANC-1 cell lines.
    View full abstract
    Download PDF (553K)
  • Microbial Mannosidation of Bioactive Chlorogentisyl Alcohol by the Marine-Derived Fungus Chrysosporium synchronum
    Keumja Yun, Chinni Mahesh Kondempudi, Hong Dae Choi, Jung Sook Kang, B ...
    Article type: Note
    2011 Volume 59 Issue 4 Pages 499-501
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.499
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    The biological transformation of the biologically active chlorogentisyl alcohol (1), isolated from the marine-derived fungus Aspergillus sp., was studied. Preparative-scale fermentation of chlorogentisyl alcohol with marine-derived fungus Chrysosporium synchronum resulted in the isolation of a new glycosidic metabolite, 1-O-(α-D-mannopyranosyl)chlorogentisyl alcohol (2). The stereostructure of the new metabolite obtained was assigned on the basis of detailed spectroscopic data analyses, chemical reaction, and chemical synthesis. Compounds 1 and 2 exhibited significant radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) with IC50 values of 1.0 and 4.7 μM, respectively. The compounds 1 and 2 were more active than the positive control, L-ascorbic acid (IC50, 20.0 μM).
    View full abstract
    Download PDF (501K)
  • Structure–Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production
    Yusaku Miyamae, Manami Kurisu, Junkyu Han, Hiroko Isoda, Hideyuki Shig ...
    Article type: Note
    2011 Volume 59 Issue 4 Pages 502-507
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.502
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1—42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure–activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.
    View full abstract
    Download PDF (826K)
  • Izumiphenazine D, a New Phenazoquinoline N-Oxide from Streptomyces sp. IFM 11204
    Mohamed S. Abdelfattah, Kazufumi Toume, Masami Ishibashi
    Article type: Note
    2011 Volume 59 Issue 4 Pages 508-510
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.508
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    A new phenazine derivative named izumiphenazine D (1), together with three known metabolites, 1-hydroxyphenazine (2), phenazine-1-carboxylic acid (3) and 6-hydroxyphenazine-1-carboxylic acid (4) has been isolated from the ethyl acetate extract of culture of Streptomyces sp. IFM 11204. The structure of 1 was established via spectroscopic methods, including 1D- and 2D-NMR measurements.
    View full abstract
    Download PDF (541K)
  • Fischerisin A and B, Cytotoxic Sesquiterpenoid-Geranylhydroquinones from Ligularia fischeri
    Wei-Dong Xie, Xia Li, Cheng-Wu Weng, Shan-Shan Liu, Kyung Ho Row
    Article type: Note
    2011 Volume 59 Issue 4 Pages 511-514
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.511
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    During the course of screening natural sesquiterpenoids for new antitumor agents, two novel compounds, fischerisin A (1) and fischerisin B (2), were isolated from the roots of Ligularia fischeri. Their structures were elucidated by interpretation of their IR, high resolution-mass spectrometry (HR-MS), 1D- and 2D-NMR data. Fischerisin A and B are the first representatives of a novel sesquiterpenoid-geranylhydroquinone hybrid, and both compounds exhibited in vitro cytotoxicity against cultured human oral epidermoid carcinoma (KB) and human breast cancer (MCF-7) cell lines with IC50 values of 9.7 and 10.2 μM, and 9.8 and 17.8 μM, respectively.
    View full abstract
    Download PDF (498K)
  • Citrinin Derivatives from the Marine-Derived Fungus Penicillium citrinum
    Li Chen, Wei Liu, Xiao Hu, Kai Huang, Jiu-Lin Wu, Qi-Qing Zhang
    Article type: Note
    2011 Volume 59 Issue 4 Pages 515-517
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.515
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Three new citrinin derivatives, penicitrinols C, D, and E (1—3), along with two known compounds, citrinin (4) and decarboxydihydrocitrinone (5), were isolated from Penicillium citrinum. Their structures were determined by spectroscopic methods and X-ray diffraction analysis. Compounds 1 and 3 demonstrated weak cytotoxicity against the HL-60 cell line.
    View full abstract
    Download PDF (681K)
  • Three New Triterpenoid Saponins from Dianthus superbus
    Jian-Guang Luo, Xia Chen, Ling-Yi Kong
    Article type: Note
    2011 Volume 59 Issue 4 Pages 518-521
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.518
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    Three new triterpenoid saponins (1—3) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were established as 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-6-O-((3S)-3-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-glucopyranosyl(1→3)][β-D-6-O-((3S)-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (2), 3-O-α-L-arabinopyranosyl-3β,16α-dihydroxyolean-12-en-23,28-dioic acid 28-O-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (3), on the basis of various spectroscopic analyses and chemical degradations.
    View full abstract
    Download PDF (513K)
  • Stereoselective Vinylogous Mukaiyama Aldol Reaction of α-Haloenals
    Yoichi Iwasaki, Ryosuke Matsui, Takahiro Suzuki, Atsuo Nakazaki, Susum ...
    Article type: Note
    2011 Volume 59 Issue 4 Pages 522-524
    Published: April 01, 2011
    Released on J-STAGE: April 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.522
    JOURNAL FREE ACCESS
    Show abstractHide abstract
    We have developed a high-yielding and stereoselective vinylogous Mukaiyama aldol reaction (VMAR) of α-haloenals. Contrary to the simple α,β-unsaturated aldehyde, α-haloenals were found to be reactive affording the corresponding VMAR adducts in excellent yields. Some transformations of VMAR adducts by Pd-mediated cross-coupling were also examined in order to demonstrate the synthetic utility of VMAR of α-haloenals.
    View full abstract
    Download PDF (535K)
Communication to the Editor
    • |<
    • <
    • 1
    • >
    • >|
feedback
 Top